EP2626346B1 - Benzo[k]fluoranthen-derivat und dieses enthaltendes organisches elektrolumineszenzelement - Google Patents

Benzo[k]fluoranthen-derivat und dieses enthaltendes organisches elektrolumineszenzelement Download PDF

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EP2626346B1
EP2626346B1 EP11830770.1A EP11830770A EP2626346B1 EP 2626346 B1 EP2626346 B1 EP 2626346B1 EP 11830770 A EP11830770 A EP 11830770A EP 2626346 B1 EP2626346 B1 EP 2626346B1
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ring
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EP2626346A4 (de
EP2626346A1 (de
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Hirokatsu Ito
Masahiro Kawamura
Yuichiro Kawamura
Yumiko Mizuki
Hiroyuki Saito
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Idemitsu Kosan Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
    • C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
    • C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
    • C07C13/62—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/22—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing two or more pyridine rings directly linked together, e.g. bipyridyl
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/20—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the material in which the electroluminescent material is embedded
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/623—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing five rings, e.g. pentacene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers

Definitions

  • the present invention relates to a benzo[k]fluoranthene derivative and an organic electroluminescence device (organic EL device) containing the benzo[k]fluoranthene derivative.
  • Patent Document 1 discloses compounds having a 1,10-phenanthroline structure or a bipyridine structure.
  • luminance, half-lifetime and luminous efficiency of organic EL devices containing these compounds described in the working examples are merely relative values on the basis of organic EL devices using comparative compounds. Actual measured values which enable one to decide whether or not these compounds realize a practically effective EL device performance are not shown.
  • Patent Documents 2 and 3 disclose anthracene compounds having two 2,2'-bipyridin-5-yl groups. Though the compounds disclosed in Patent Document 3 improve the lifetime, a driving voltage thereof tends to become high.
  • Patent Document 4 discloses anthracene compounds having a 1,10-phenanthrolinyl group, a more improvement in the lifetime is desired.
  • Patent Documents 5 and 6 describe that benzo[k]fluoranthene compounds having a benzoimidazolyl group or a substituent analogous thereto are used as an electron transporting material.
  • Patent Document 7 discloses certain benzofluoranthene compounds and their use in organic LEDs.
  • An object of the present invention is to solve the problems of the compounds as described above and to provide a novel compound which reduces a driving voltage of an organic EL device and which makes it possible to realize light emission with high efficiency and long lifetime.
  • the present inventors made extensive and intensive investigations. As a result, it has been found that a benzo[k]fluoranthene derivative as described below achieves the foregoing object, leading to accomplishment of the present invention. That is, the present invention relates to a benzo[k]fluoranthene derivative, a device for organic electroluminescence device, and an organic EL device containing the subject derivative as described below.
  • each of R 1 to R 12 independently represents a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 8 ring carbon atoms, a substituted silyl group having 3 to 30 carbon atoms, a cyano group, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, provided that at least one of R 1 to R 12 is a group represented by the following formula (1a). -L-(-HAr) n (1a)
  • L represents a single bond, a divalent to tetravalent residue of a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 ring carbon atoms, a divalent to tetravalent residue of a substituted or unsubstituted heterocyclic ring having 5 to 30 ring atoms, or a divalent to tetravalent residue of a ring formed through bonding of from 2 to 3 rings selected from the foregoing aromatic hydrocarbon ring and heterocyclic ring via a single bond; n represents an integer of from 1 to 3; and HAr represents a group represented by the following formula (2).
  • each of X 1 to X 8 independently represents a nitrogen atom or CR 13 , and at least one of X 1 to X 8 is CR 13 ; and each of R 13 s independently represents a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 8 ring carbon atoms, a substituted silyl group having 3 to 30 carbon atoms, a cyano group, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, a substituted or unsubstituted, mono- or dialkylamino group having 1 to 20 carbon atoms, a substituted
  • each of R 21 to R 66 independently represents a hydrogen atoms, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 8 ring carbon atoms, a substituted silyl group having 3 to 30 carbon atoms, a cyano group, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, substituted or unsubstituted mono- or dialkylamino group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to
  • R 1 to R 3 , R 5 to R 12 , HAr, L, and n are the same as defined above.
  • the organic EL device containing the benzo[k]fluoranthene derivative of the present invention is low in a driving voltage and exhibits light emission with high efficiency and long lifetime.
  • the benzo[k]fluoranthene derivative of the present invention is represented by the following formula (1).
  • each of R 1 to R 12 independently represents a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 8 ring carbon atoms, a substituted silyl group having 3 to 30 carbon atoms, a cyano group, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
  • at least one of R 1 to R 12 is a group represented by the following formula (1a). -L-(-HAr) n (1a)
  • R 1 to R 12 may be the same as or different from each other, and the respective groups represented by each of them are as follows.
  • the halogen atom is selected from a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, with a fluorine atom being preferable.
  • alkyl group having 1 to 10 (preferably 1 to 6, and more preferably 1 to 4) carbon atoms
  • an ethyl group, a methyl group, an isopropyl group, an n-propyl group, an n-butyl group, an s-butyl group, a t-butyl group, an isobutyl group, a pentyl group (inclusive of structural isomerism), a hexyl group (inclusive of structural isomerism), and the like are preferable.
  • Examples of the substituted alkyl group include alkyl groups having a substituent as described later.
  • cycloalkyl group having 3 to 8 (preferably 3 to 6) ring carbon atoms a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group are preferable.
  • substituted cycloalkyl group include cycloalkyl groups having a substituent as described later.
  • the substituted silyl group having 3 to 30 carbon atoms includes an alkylsilyl group having 3 to 30 carbon atoms (inclusive of mono-, di- and trialkylsilyl groups) and an arylsilyl group having 8 to 30 carbon atoms (inclusive of an aryldialkylsilyl group, a diarylalkylsilyl group, and a triarylsilyl group).
  • alkylsilyl group having 3 to 30 (preferably 3 to 20, and more preferably 3 to 10) carbon atoms examples include a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, and so on.
  • Examples of the arylsilyl group having 8 to 30 carbon atoms include a triphenylsilyl group, a phenyldimethylsilyl group, a t-butyldiphenylsilyl group, a tritolylsilyl group, a trixylylsilyl group, a trinaphthylsilyl group, and so on.
  • the alkoxy group having 1 to 20 (preferably 1 to 10, and more preferably 1 to 6) carbon atoms is a group represented by -OY, and specific examples, preferred examples, and more preferred examples of Y are selected from the groups described above regarding the alkyl group.
  • Examples of the substituted alkoxy include alkoxy groups having a substituent as described later.
  • Examples of the aryl group having 6 to 30 (preferably 6 to 20, and more preferably 6 to 12) ring carbon atoms include a phenyl group, a naphthyl group, a phenanthryl group, a biphenyl group, a terphenyl group, an anthryl group, a pyrenyl group, a chrysenyl group, a benzophenanthryl group, a benzanthryl group, a benzochrysenyl group, a fluorenyl group, a fluoranthenyl group, a naphthacenyl group, and so on.
  • a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-biphenyl group, a 3-biphenyl group, a 4-biphenyl group, a 9-phenanthryl group, and a 1-pyrenyl group are more preferable, with a phenyl group being especially preferable.
  • Examples of the substituted aryl group include aryl groups having a substituent as described later.
  • a 4-tolyl group, a 4-fluorophenyl group, a 4-trifluoromethylphenyl group, a 4-t-butylphenyl group, a 4-trimethylsilylphenyl group, a 4-methoxyphenyl group, a 4-cyanophenyl group, a 3-tolyl group, a 3-fluorophenyl group, a 3-trifluoromethylphenyl group, a 3-t-butylphenyl group, a 3-trimethylsilylphenyl group, a 3-methoxyphenyl group, a 3-cyanophenyl group, a 2-tolyl group, a 2-fluorophenyl group, a 2-trifluoromethylphenyl group, a 2-t-butylphenyl group, a 2-trimethylsilylphenyl group, a 2-methoxyphenyl group, a 2-cyanophenyl group, and the like are preferable.
  • the aryloxy group having 6 to 20 (preferably 6 to 10) ring carbon atoms is a group represented by -OAr, and Ar is selected from the groups and preferred groups described above regarding the aryl group.
  • Examples of the substituted aryloxy group include aryloxy groups having a substituent as described later.
  • heterocyclic group having 5 to 30 (preferably 5 to 20, and more preferably 5 to 12) ring atoms examples include a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, an indolyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, an acridinyl group, a pyrrolidinyl group, a dioxanyl group, a piperidinyl group, a morpholyl group, a piperazinyl group, a carbazolyl group, a furanyl group, a thiophenyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a furazanyl group, a benzoxazolyl group, a thiazolyl group,
  • a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 8 ring carbon atoms, and a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms are preferable.
  • R 7 and R 12 are a hydrogen atom or the substituent described above.
  • the substituent is preferably a group selected from a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-biphenyl group, a 3-biphenyl group, a 4-biphenyl group, a 9-phenanthryl group, a 1-pyrenyl group, a 4-tolyl group, a 4-fluorophenyl group, a 4-trifluoromethylphenyl group, a 4-t-butylphenyl group, a 4-trimethylsilylphenyl group, a 4-methoxyphenyl group, a 4-cyanophenyl group, a 3-tolyl group, a 3-fluorophenyl group, a 3-trifluoromethylphenyl group, a 3-t-butylphenyl group, a 3-trimethyls
  • L represents a single bond, a divalent to tetravalent residue of a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 ring carbon atoms, a divalent to tetravalent residue of a substituted or unsubstituted heterocyclic ring having 5 to 30 ring atoms, or a divalent to tetravalent residue of a ring formed through bonding of 2 to 3 rings selected from the foregoing aromatic hydrocarbon ring and heterocyclic ring via a single bond.
  • the divalent to tetravalent (preferably divalent or trivalent, and more preferably divalent) residue of an aromatic hydrocarbon ring having 6 to 30 (preferably 6 to 20, and more preferably 6 to 12) ring carbon atoms is a divalent to tetravalent group obtained by eliminating 1 to 3 hydrogen atoms from the aryl group having 6 to 30 ring carbon atoms as described regarding R 1 to R 12 .
  • the divalent to tetravalent (preferably divalent or trivalent, and more preferably divalent) residue of a heterocyclic ring having 5 to 30 (preferably 5 to 20, and more preferably 5 to 12) ring atoms is a divalent to tetravalent group obtained by eliminating 1 to 3 hydrogen atoms from the heterocyclic group having 5 to 30 ring atoms as described regarding R 1 to R 12 .
  • a divalent to tetravalent residue of a ring selected from pyridine, pyrimidine, pyridazine, pyrazine, quinoline, isoquinoline, and triazine is preferable; a pyridinediyl group, a pyrimidinediyl group, a pyridazinediyl group, a pyrazinediyl group, a quinolinediyl group, and a triazinediyl group are more preferable; and a pyrimidine-2,5-diyl group, a pyrimidine-2,4-diyl group, a pyridazine-3,6-diyl group, a pyrazine-2,5-diyl group, a pyridine-2,4-diyl group, a pyridine-2,5-diyl group, a pyridine-2,6-diyl group, a
  • the divalent to tetravalent residue of a ring formed through bonding of 2 to 3 rings selected from the aromatic hydrocarbon ring and heterocyclic ring via a single bond is preferably a divalent to tetravalent residue of the following compounds. Two to four free bonds may be bounded to any position of the aromatic hydrocarbon ring and the heterocyclic ring.
  • Each of the two free bonds may be bonded at any position of the benzene ring in which each free bond is contained, and either of the two free bonds may be bonded to the benzofluoranthene skeleton or may be bonded to HAr.
  • Either of the two free bonds may be bonded to the benzofluoranthene skeleton or may be bonded to HAr.
  • n is an integer of 1 to 3, and preferably 1.
  • n is 2 or 3
  • two or three HArs may be the same or different.
  • HAr is a group represented by the following formula (2).
  • Each of X 1 to X 8 independently represents a nitrogen atom or CR 13 , and at least one of X 1 to X 8 is CR 13 ; and each of R 13 s independently represents a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 8 ring carbon atoms, a substituted silyl group having 3 to 30 carbon atoms, a cyano group, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, a substituted or unsubstituted mono- or dialkylamino group having 1 to 20 carbon atoms, a substituted or unsubsti
  • halogen atom examples of the halogen atom, the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, the substituted or unsubstituted cycloalkyl group having 3 to 8 ring carbon atoms, the substituted silyl group having 3 to 30 carbon atoms, the cyano group, the substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, the substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and the substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms are the same as those described above regarding R 1 to R 12 .
  • the alkylthio group having 1 to 20 carbon atoms is represented by -SY 1
  • the mono- or dialkylamino group having 1 to 20 carbon atoms is represented by -NHY 2 or -NY 2 Y 3 , respectively.
  • Y 1 , Y 2 , and Y 3 are the same as Y described above.
  • Examples of the optional substituent of the alkylthio group or the mono- or dialkylamino group include substituents as described later.
  • the arylthio group having 6 to 20 (preferably 6 to 10) ring carbon atoms is a group represented by -SAr 1 , and Ar 1 is the same as Ar described above.
  • Examples of the substituted arylthio group include aryloxy groups having a substituent as described later.
  • the mono- or diarylamino group having 6 to 40 (preferably 6 to 20) ring carbon atoms is represented by -NHAr 1 or -NAr 2 Ar 3 , respectively.
  • Ar 1 , Ar 2 , and Ar 3 are the same as Ar described above.
  • Examples of the substituted mono- or diarylamino group include mono- or diarylamino groups having a substituent as described later.
  • a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms are preferable; and a hydrogen atom, a phenyl group, a 2-, 3- or 4-methoxyphenyl group, a 2-, 3- or 4-trimethylsilylphenyl group, a 2-, 3- or 4-trifluoromethylphenyl group, a 2-, 3- or 4-cyanophenyl group, a 2-, 3- or 4-fluorophenyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 2-pyrimidinyl group, a 2-triazinyl group, a 2-bipyridyl group, a 9-phenanthryl group,
  • Two or more R 13 s may be bonded to each other to form a substituted or unsubstituted, saturated or unsaturated group capable of forming a part of the ring.
  • each of X 4 and X 5 is CR 13
  • the R 13 s are bonded to each other to form a substituted or unsubstituted methylene group is excluded.
  • Two or more R 13 s may not be adjoined to each other, and for example, in the case where each of X 1 and X 4 is CR 13 , the two R 13 s may be bonded to each other to form a ring-forming substituted or unsubstituted, saturated or unsaturated divalent group.
  • each of X 1 , X 2 , and X 3 is CR 13
  • the three R 13 s may be bonded to each other to form a ring-forming substituted or unsubstituted, saturated or unsaturated trivalent group.
  • the ring-forming substituted or unsubstituted, saturated or unsaturated group may contain one or two or more hetero atoms selected from a nitrogen atom, an oxygen atom, and a sulfur atom in a main skeleton thereof.
  • Examples of the ring in which two or more R 13 s are bonded to each other include a carbon 6-membered ring, a carbon 7-membered ring, a hetero 5-membered ring containing one oxygen atom, with the other being carbon atoms, a hetero 6-membered ring containing one oxygen atom, with the other being carbon atoms, a hetero 7-membered ring containing one oxygen atom, with the other being carbon atoms, a hetero 5-membered ring containing one nitrogen atom, with the other being carbon atoms a hetero 6-membered ring containing one nitrogen atom, with the other being carbon atoms, a hetero 5-membered ring containing one sulfur atom, with the other being carbon atoms, a hetero 5-membered ring containing one oxygen atom and one nitrogen atom, with the other being carbon atoms, and so on.
  • a ring number is preferably 1 to 8, more preferably 1 to 4, and especially preferably 1 or 2. In the case where two or more rings are formed, these rings may be the same or different.
  • Examples of the group represented by the formula (2) in the case where two or more R 13 s are bonded to each other to form a ring (optional substituents are omitted) include residues of the following compounds.
  • the above residues are preferably the following residues.
  • the free bond may be bonded at any position of the aromatic ring containing it (provided that a nitrogen atom is excluded).
  • HAr in the formula (2) is preferably represented by any of the following formulae (3) to (7).
  • each of R 21 to R 66 is a hydrogen atom, a halogen atom, or a group selected from the groups described regarding R 13 .
  • two or more of R 21 to R 28 may be bonded to each other to form a ring-forming substituted or unsubstituted, saturated or unsaturated group, provided that any one of R 21 to R 28 , preferably one of R 21 , R 22 , R 24 , R 25 , R 27 , and R 28 , and more preferably one of R 21, R 22 , R 27 , and R 28 is a single bond and is bonded to L, and the case where R 24 and R 25 are bonded to each other to form a substituted or unsubstituted methylene group is excluded.
  • R 31 to R 38 may be bonded to each other to form a ring-forming substituted or unsubstituted, saturated or unsaturated group, provided that any one of R 31 to R 38 , and preferably one of R 31 and R 38 is a single bond and is bonded to L.
  • two or more of R 41 to R 47 may be bonded to each other to form a ring-forming saturated or unsaturated group, provided that any one of R 41 to R 47 , and preferably one of R 41 , R 43 , and R 47 is a single bond and is bonded to L.
  • two or more of R 51 to R 57 may be bonded to each other to form a ring-forming substituted or unsubstituted, saturated or unsaturated group, provided that any one of R 51 to R 57 , and more preferably one of R 51 , R 52 , and R 57 is a single bond and is bonded to L, and the case where R 53 and R 54 are bonded to each other to form a substituted or unsubstituted methylene group is excluded.
  • two or more of R 61 to R 66 may be bonded to each other to form a ring-forming substituted or unsubstituted, saturated or unsaturated group, provided that any one of R 61 to R 66 , and preferably one of R 61 , R 62 , and R 66 is a single bond and is bonded to L.
  • -L-(HAr) n represented by the formula (1a) is preferably bonded at any one of the 3-, 4-, 7- and 12-positions, and especially preferably bonded at the 3- or 4-position of the benzo[k]fluoranthene skeleton of the formula (1).
  • the benzo[k]fluoranthene derivative represented by the formula (1) is preferably represented by the following formula (8).
  • R 1 to R 3 , R 5 to R 12 , HAr, L, and n are the same as those in the formula (1).
  • the benzo[k]fluoranthene derivative represented by the formula (1) is more preferably represented by the following formula (9).
  • R 1 to R 3 , R 5 , R 6 , R 8 to R 11 , HAr, L, and n are the same as those in the foregoing formula (1).
  • L of the benzo[k]fluoranthene derivative represented by the formula (1), (8) or (9) is a single bond, since a distance between the benzofluoranthene skeleton (charge transporting site) and -(HAr) n (electron injecting site) is short, it may be considered that the charge transfer in the molecule becomes smooth (the electron can transfer to the charge transport site within a short period of time). In consequence, it may be considered that the driving voltage is reduced.
  • L of the benzo[k]fluoranthene derivative of the present invention is a divalent to tetravalent residue of a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 ring carbon atoms, a divalent to tetravalent residue of a substituted or unsubstituted heterocyclic ring having 5 to 30 ring atoms, or a divalent to tetravalent residue of a ring formed through bonding of 2 to 3 rings selected from the foregoing aromatic hydrocarbon ring and heterocyclic ring via a single bond, since a distance between the benzo[k]fluoranthene skeleton and -(HAr) n is long, it may be considered that the electronic participation of the benzofluoranthene skeleton and -(HAr) n .
  • each of R 7 and R 12 independently represents an aryl group having 6 to 30 ring carbon atoms (preferably from 6 to 20, and more preferably from 6 to 12), and it is especially preferable that both of R 7 and R 12 are a phenyl group.
  • R 7 and R 12 is an aryl group, it may be considered that the planarity of the benzo[k]fluoranthene skeleton is enhanced.
  • benzo[k]fluoranthene derivative whose planarity has been enhanced, it may be considered that overlap of the molecules each other becomes large, so that the distance between the molecules becomes short, whereby charge transporting properties of the benzo[k]fluoranthene derivative can be more enhanced.
  • the hydrogen atoms of the benzo[k]fluoranthene derivative of the present invention include light hydrogen and heavy hydrogen.
  • the "ring carbon atoms” means a carbon atom constituting a saturated ring, an unsaturated ring, or an aromatic ring.
  • the "ring atoms” means a carbon atom and a hetero atom constituting a hetero saturated ring, a hetero unsaturated ring, or a hetero aromatic ring.
  • the optional substituent in the case of referring to "substituted or unsubstituted " is a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 8 ring carbon atoms, a substituted or unsubstituted silyl group having 3 to 30 carbon atoms, a cyano group, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, a substituted or unsubstituted mono- or dialkylamino group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and a
  • Specific examples thereof include a fluorine atom, a methyl group, a 1-, 2- or 3-pyridyl group, a trimethylsilyl group, a methoxy group, a cyano group, a 1- or 2-naphthyl group, a 2-, 3- or 4-methoxyphenyl group, a 2-, 3- or 4-trimethylsilylphenyl group, a 2-, 3- or 4-cyanophenyl group, a 2-pyrimidyl group, a 2-triazinyl group, a 3- or 4-bipyridyl group, and so on.
  • the benzo[k]fluoranthene derivative of the present invention as described above in detail has high charge transporting properties because it contains a benzo[k]fluoranthene skeleton having high planarity, and the molecules well overlap each other.
  • the benzo[k]fluoranthene skeleton has higher charge transporting properties than, for example, a fluoranthene skeleton because of its high planarity.
  • the benzo[k]fluoranthene skeleton has high charge durability, and in the case of using the benzo[k]fluoranthene derivative of the present invention for an organic EL device, an enhancement of the lifetime can be expected. Though there may be the case where a hole flows to the side of an electron injecting layer, since the benzo[k]fluoranthene derivative of the present invention has hole resistance, it may be considered that it can prevent deterioration of the device.
  • the benzo[k]fluoranthene derivative of the present invention has a benzo[k]fluoranthene skeleton, an affinity (Af) becomes large, and for example, in the case where it is used for an electron transporting layer, an interaction with an adjoining metal complex layer or reducing dopant layer becomes high, so that it can be expected that satisfactory electron injecting properties are revealed. From the foregoing reasons, it may be considered that the benzo[k]fluoranthene derivative of the present invention lowers the driving voltage of the organic EL device.
  • a heterocyclic ring such as a pyridine ring and the like, can coordinate to a metal atom using a lone pair on a nitrogen atom thereof, it may be considered that an affinity with an electrode becomes strong. It may be considered that in the bipyridine structure or phenanthroline structure contained in HAr of the benzo[k]fluoranthene derivative of the present invention, two nitrogen atoms are present at positions at which a chelate with a lithium ion or the like is easily formed. In particular, since two nitrogen atoms of the bipyridine structure are rotatable around the single bond, it may be considered that a distance therebetween can be varied depending upon an ionic radius of a metal ion to be coordinated.
  • HAr contains two nitrogen atoms at positions at which a chelate with a metal ion is easily formed, it is easy to capture the metal ion on the cathode side. Therefore, it may be considered that HAr can enhance the electron injecting properties of the organic EL device as compared with a benzoimidazolyl group and other heterocyclic groups.
  • diazafluorenyl group in view of the fact that a 5-membered ring structure connected with a methylene group in the center is taken, it may be considered that a distance between the two nitrogen atoms increases as compared with the case of the bipyridine structure, and for example, it becomes hard to capture an ion having a smaller ionic radius, such as a lithium ion or the like.
  • the benzo[k]fluoranthene derivative of the present invention is a compound having a benzo[k]fluoranthene structure and a bipyridine structure or an analogous structure thereto in one molecule, and it is a compound having excellent charge transporting properties, charge durability and electron injecting properties at the same time.
  • the benzo[k]fluoranthene derivative of the present invention is used preferably as a material for organic EL device, and more preferably as an electron injecting material or electron transporting material of an organic EL device. This is because HAr mediates an electron transfer from the adjoining layer. Also, it may be considered that the benzo[k]fluoranthene derivative of the present invention can be suitably used as a triplet energy blocking material for the reasons as described later.
  • the benzo[k]fluoranthene skeleton that is a basic skeleton of the benzo[k]fluoranthene derivative of the present invention has high triplet energy and high confinement effect of a triplet exciton, and therefore, it may be considered that for example, by utilizing it as a material of a blocking layer coming into contact with a light emitting layer of an organic EL device, a TTF (triplet-triplet fusion) phenomenon can be promoted.
  • the benzo[k]fluoranthene skeleton that is a basic skeleton of the benzo[k]fluoranthene derivative of the present invention has such a characteristic feature that molecular stacking in a thin film is enhanced due to a height planarity, whereby electron transporting properties become large, and therefore, it may be considered that it is able to promote electron injection into the light emitting layer and enhance recombination efficiency in the light emitting layer, thereby efficiently causing the TTF phenomenon.
  • the benzo[k]fluoranthene derivative of the present invention contains HAr that is a nitrogen-containing heterocyclic ring with high electron injecting properties from a metal-containing layer, such as an electrode and the like, it may be considered that it is able to realize an organic EL device with a low driving voltage without further laminating an electron injecting layer.
  • the benzo[k]fluoranthene derivative of the present invention is a compound provided with both of an electron injection/transport function and a triplet energy blocking function (triplet blocking function).
  • the benzo[k]fluoranthene derivative of the present invention is a compound containing a structural site having a triplet blocking functional (triplet blocking structural site) and a structural site having an electron injecting/transporting function.
  • the structural site refers to an individual cyclic structure (single ring or condensed polycyclic ring exclusive of a substituent) which is contained in a compound.
  • the triplet blocking structural site refers to a structural site having the lowest (smallest) triplet energy among the structural sites contained in a compound.
  • the triplet blocking structural site is a structural site which determines chiefly the triplet energy of a compound.
  • the triplet energy of the triplet blocking structural site refers to triplet energy of an independent cyclic structure in which hydrogen is substituted at a bonding position of the respective structural sites each other exclusive of a substituent.
  • the triplet blocking structural site must be a condensed polycyclic aromatic hydrocarbon compound. Reasons for this are described below.
  • the transition state of the condensed ring composed of a hydrocarbon is based on the ⁇ - ⁇ * transition in which an electron cloud of the cyclic structure participates. An expanse of this ⁇ electron cloud is small, and its influences against the excited state of the light emitting layer are small.
  • the transition state of the case of having a lone pair in the structural site in view of the fact that the lone pair participates therein, a strong interaction with a triplet exciton produced in the light emitting layer is generated, thereby promoting deactivation of the triplet exciton of a host.
  • the triplet blocking structural site of the blocking material must be a condensed ring composed of a hydrocarbon which forms an excited triplet state chiefly on the basis of the ⁇ - ⁇ * transition.
  • the triplet energy of the blocking material is larger than the triplet energy of the host of the light emitting layer.
  • the triplet blocking function of the blocking material is determined chiefly by the triplet blocking structural site.
  • the triplet energy is transferred to the structural site having the lowest triplet energy among the respective structural sites of the blocking material.
  • the triplet blocking structural site having the lowest triplet energy among the respective structural sites is a condensed polycyclic aromatic hydrocarbon compound
  • the blocking material effectively exhibits the triplet blocking function. From the foregoing reasons, in the case where the structural site having the lowest (smallest) triplet energy among the structural sites contained in a compound is not constituted of carbon and hydrogen, the subject compound does not have a triplet blocking structural site.
  • the TTF phenomenon is hereunder briefly described.
  • the TTF phenomenon is a phenomenon in which a singlet exciton is produced due to collision and fusion of triplet excitons.
  • the blocking layer containing the benzo[k]fluoranthene derivative of the present invention it is preferable to allow the blocking layer containing the benzo[k]fluoranthene derivative of the present invention to adjoin to a light emitting layer of a fluorescent device. It may be considered that when the blocking layer containing the benzo[k]fluoranthene derivative of the present invention is used for a fluorescent device, the TTF phenomenon is caused, thereby enabling one to realize an organic EL device with high efficiency.
  • the blocking layer of the present invention is a layer having a blocking function against the triplet energy, and it is different in the function from a hole blocking layer and a charge blocking layer.
  • the blocking layer containing the benzo[k]fluoranthene derivative of the present invention, the electron injecting layer, or the electron transporting layer further contains a reducing dopant.
  • Examples of the reducing dopant include a donating metal, a donating metal compound, and a donating metal complex. These reducing dopants may be used singly or in combination of two or more kinds thereof.
  • the reducing dopant is a material for donating an electron (referred to as "electron donating material").
  • This electron donating material is a material which interacts with other organic material contained in the blocking layer, the electron injecting layer, or the electron transporting layer together with the electron donating material, or an organic material constituting a layer adjoining to the blocking layer, the electron injecting layer, or the electron transporting layer, thereby producing a radical anion, or a material having an electron donating radical.
  • the donating metal refers to a metal having a work function of not more than 3.8 eV, and it is preferably an alkali metal, an alkaline earth metal, or a rate earth metal, and more preferably Cs, Li, Na, Sr, K, Mg, Ca, Ba, Yb, Eu, or Ce.
  • the donating metal compound refers to a compound containing the donating metal, and it is preferably a compound containing an alkali metal, an alkaline earth metal, or a rate earth metal, and more preferably a halide, an oxide, a carbonate, or a borate of such a metal.
  • Examples thereof include compounds represented by MO x (M is a donating metal, and x is 0.5 to 1.5), MF x (x is 1 to 3), or M(CO 3 ) x (x is 0.5 to 1.5).
  • the donating metal complex refers to a complex of the donating metal, and it is preferably an organic metal complex of an alkali metal, an alkaline earth metal, or a rare earth metal.
  • the donating metal complex is an organometallic complex represented by the following formula (I). M-(-Q) n (I)
  • M is a donating metal
  • Q is a ligand, and preferably a carboxylic acid derivative, a diketone derivative, or a quinoline derivative
  • n is an integer of 1 to 4.
  • the donating metal complex examples include tungsten paddlewheels described in JP-A-2005-72012 , and so on. Furthermore, phthalocyanine compounds having an alkali metal or an alkaline earth metal as a central metal as described in JP-A-11-345687 , or the like can also be used as the donating metal complex.
  • the foregoing reducing dopant is preferably one or more kinds selected from the group consisting of an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal oxide, an alkali metal halide, an alkaline earth metal oxide, an alkaline earth metal halide, a rare earth metal oxide, a rare earth metal halide, an organic complex of an alkali metal, an organic complex of an alkaline earth metal, and an organic complex of a rare earth metal, and more preferably an 8-quinolinol complex of an alkali metal.
  • the triplet energy of a compound constituting the blocking layer composed of the benzo[k]fluoranthene derivative of the present invention must be higher than the triplet energy of a host chiefly constituting the light emitting layer.
  • the benzo[k]fluoranthene derivative of the present invention, which is contained in the blocking layer, and the host and the dopant contained in the light emitting layer satisfy the following expressions (1) and (2).
  • E T h, E T b, and E T d represent triplet energies of the host material, the nitrogen-containing heterocyclic derivative of the blocking layer, and the dopant, respectively.
  • Fig. 1 is a diagrammatic configuration of an organic EL device showing an example of embodiments of the present invention.
  • Fig. 2 schematically expresses the lowest excited singlet energy level and the lowest excited triplet energy level of each layer.
  • the triplet energy refers to a difference between the energy in the lowest excited triplet state and the energy in the ground state
  • the singlet energy also called "energy gap" refers to a difference between the energy in the lowest excited singlet state and the energy in the ground state.
  • the organic EL device of the present invention is a device provided with an anode, a light emitting layer, an electron transporting zone, and a cathode in this order, and in the organic EL device shown in Fig. 1 , a hole transporting zone 50, a light emitting layer 20, an electron transporting zone 30, and a cathode 40 are successively laminated in this order from an anode 10. It is preferable that the hole transporting zone 50 is provided between the anode 10 and the light emitting layer 20. In the embodiment shown in Fig. 2 , a configuration in which the electron transporting zone is composed of only a blocking layer is shown.
  • the electron transporting zone includes a blocking layer, and the embodiment of only a blocking layer does not exclude insertion of an electron injecting layer having high injection properties.
  • an electron injecting layer When an electron injecting layer is formed, general compounds which have been conventionally used for an electron injecting layer can be used, and a heterocyclic ring-containing compound is preferable.
  • a hole injected from the anode is injected into the light emitting layer through the hole transporting zone, and an electron injected from the cathode is injected into the light emitting layer through the electron transporting zone. Thereafter, the hole and the electron are recombined in the light emitting layer, thereby producing a singlet exciton and a triplet exciton.
  • the recombination occurs on the host molecule and the case where the recombination occurs on the dopant molecule. In the present embodiment, as shown in Fig.
  • the triplet exciton which has been recombined and produced on the dopant molecule rapidly causes energy transfer to the host molecule. That is, the triplet excitons efficiently collide with each other on the host by the TTF phenomenon without causing transfer of the triplet exciton of the host to the dopant, thereby producing a singlet exciton. Furthermore, since a singlet energy E S d of the dopant is smaller than a singlet energy E S h of the host, the singlet exciton produced by the TTF phenomenon causes energy transfer from the host to the dopant, thereby contributing to fluorescent light emission of the dopant.
  • the transition from the excited triplet state to the ground state is forbidden, and in such transition, the triplet exciton did not cause optical energy deactivation but caused thermal deactivation.
  • the triplet exciton efficiently produces a singlet exciton due to mutual collision thereof before causing thermal deactivation, thereby enhancing the luminous efficiency.
  • the blocking layer has such a function that by preventing diffusion of a triplet exciton produced in the light emitting layer into the electron transporting zone and confining the triplet exciton within the light emitting layer, the density of the triplet exciton is increased, thereby efficiently causing the TTF phenomenon.
  • the triplet energy E T b of the compound constituting the blocking layer is larger than E T h and furthermore, larger than E T d. Since the blocking layer prevents the diffusion of the triplet exciton produced in the light emitting layer into the electron transporting zone, the triplet exciton of the host efficiently becomes a singlet exciton within the light emitting layer, and the singlet exciton transfers to the dopant, thereby causing optical energy deactivation.
  • a material which forms the blocking layer is the benzo[k]fluoranthene derivative of the present invention. Since the benzo[k]fluoranthene derivative of the present invention has hole resistance, it is hardly deteriorated, thereby prolonging the lifetime of the device.
  • the blocking layer containing the benzo[k]fluoranthene derivative of the present invention can also play a role as an electron injecting/transporting function, the electron injected in the blocking material more easily donates an electron via an electron transport structural site. That is, in view of the fact that the electron injected in the blocking material transfers to a structural site having a high LUMO level, it contributes to the electron injection into the light emitting layer.
  • a low-work function metal-containing layer may be provided between the electron transporting zone and the cathode as described above.
  • the low-work function metal-containing layer refers to a layer containing a low-work function metal or a low-work function metal compound.
  • the low-work function metal-containing layer may be formed of only a low-work function metal or a low-work function metal compound, or may be formed by adding, as a donor, a low-work function metal, a low-work function metal compound, or a low-work function metal complex to the material used for the electron transporting layer.
  • the low-work function metal refers to a metal having a work function of not more than 3.8 eV
  • the metal having a work function of not more than 3.8 eV include an alkali metal, an alkaline earth metal, and so on.
  • the alkali metal include Li, Na, K, Cs, and so on.
  • the alkaline earth metal include Mg, Ca, Sr, Ba, and so on.
  • Other examples include Yb, Eu, Ce, and so on.
  • oxides, halides, carbonates or borates of low-work function metal are preferable.
  • the halide include a fluoride, a chloride, and a bromide, with a fluoride being preferable.
  • the low-work function metal complex is a complex of a low-work function metal, and organometallic complexes of an alkali metal, an alkaline earth metal, or a rare earth metal are preferable.
  • the enhancement of the efficiency to be brought by utilizing the TTF phenomenon is remarkable in a blue fluorescent layer.
  • the luminous efficiency can be enhanced by confining the triplet energy within the light emitting layer.
  • the light emitting layer of the organic EL device of the present invention preferably contains at least one kind of an anthracene derivative represented by the following formula (4) or a pyrene derivative represented by the following formula (5) as a host.
  • the anthracene derivative is represented by the following formula (4):
  • Each of Ar 11 and Ar 12 independently represents a substituted or unsubstituted monocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted condensed ring group having 8 to 50 ring atoms, or a group constituted of a combination of a monocyclic group and a condensed ring group.
  • Each of R 101 to R 108 independently represents a group selected from a hydrogen atom, a substituted or unsubstituted monocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted condensed ring group having 8 to 50 ring atoms; a group constituted of a combination of a monocyclic group and a condensed ring group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms; a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms; a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms; a substituted or unsubstituted silyl group, a halogen atom, and
  • the monocyclic ring refers to a group constituted of only a non-condensed ring.
  • the monocyclic group having 5 to 50 (preferably 5 to 30, and more preferably 5 to 20) ring atoms include an aromatic group, such as a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, and the like; and a heterocyclic group, such as a pyridyl group, a pyrazyl group, a pyrimidyl group, a triazinyl group, a furyl group, a thienyl group, and the like, with a phenyl group, a biphenyl group, and a terphenyl group being preferable.
  • an aromatic group such as a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, and the like
  • a heterocyclic group such as a pyridyl group, a pyrazyl group, a pyrimidyl group,
  • the condensed ring group refers to a group having two or more ring structures condensed therein.
  • condensed ring group having 8 to 50 (preferably 8 to 30, and more preferably 8 to 20) ring atoms include a condensed aromatic ring group, such as a naphthyl group, a phenanthryl group, an anthryl group, a chrysenyl group, a benzoanthryl group, a benzophenanthryl group, a triphenylenyl group, a benzochrysenyl group, an indenyl group, a fluorenyl group, a 9,9-dimethylfluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a fluoranthenyl group, a benzofluoranthenyl group, and the like; and a condensed heterocyclic group, such as a benzofuranyl group, a benzothiophenyl group, an indolyl group, a dibenzofuranyl group
  • alkyl group having 1 to 50 carbon atoms the cycloalkyl group having 3 to 50 ring carbon atoms, the alkoxy group having 1 to 50 carbon atoms, an aryloxy group having 6 to 50 ring carbon atoms, and the substituted or unsubstituted silyl group are the same as those in the formula (1).
  • the aralkyl group having 7 to 50 carbon atoms is represented by -Y-Z.
  • Y include an alkylene corresponding to the alkyl as described above; and examples of Z include the aryl as described above.
  • the aryl moiety thereof has 6 to 49 (preferably 6 to 30, more preferably 6 to 20, and especially preferably 6 to 12) carbon atoms; the alkyl moiety thereof has 1 to 44 (preferably 1 to 30, more preferably 1 to 20, still more preferably 1 to 10, and especially preferably 1 to 6) carbon atoms; and examples thereof include a benzyl group, a phenylethyl group, and a 2-phenylpropan-2-yl group.
  • the optional substituent of the terms "substituted or unsubstituted" in each of Ar 11 , Ar 12 , and R 101 to R 108 is preferably a monocyclic group, a condensed ring group, an alkyl group, a cycloalkyl group, a silyl group, an alkoxy group, a cyano group, or a halogen atom (especially fluorine), and especially preferably a monocyclic group or a condensed ring group.
  • Examples of preferred specific substituents are the same as each of the groups in the formula (4) and as each of the groups in the formula (1).
  • the anthracene derivative represented by the formula (4) is preferably any of the following anthracene derivatives (A), (B) and (C), and it is selected depending upon the constitution of the organic EL device to be applied or the required properties.
  • the anthracene derivative is one represented by the formula (4) wherein each of Ar 11 and Ar 12 independently represents a substituted or unsubstituted condensed ring group having 8 to 50 ring atoms.
  • the anthracene derivative can be separated into the case where Ar 11 and Ar 12 are the same substituted or unsubstituted condensed ring group and the case where Ar 11 and Ar 12 are different substituted or unsubstituted condensed ring groups.
  • the anthracene derivative represented by the formula (4) wherein Ar 11 and Ar 12 are different substituted or unsubstituted condensed ring groups (inclusive of position isomers) is especially preferable, and specific examples of the condensed ring are those described above. Above all, a naphthyl group, a phenanthryl group, a benzanthryl group, a 9,9-dimethylfluorenyl group, and a dibenzofuranyl group are preferable.
  • the subject anthracene derivative is one represented by the formula (4) wherein one of Ar 11 and Ar 12 is a substituted or unsubstituted monocyclic group having 5 to 50 ring atoms and the other is a substituted or unsubstituted condensed ring group having 8 to 50 ring atoms.
  • a preferred embodiment is one in which Ar 12 is a naphthyl group, a phenanthryl group, a benzoanthryl group, a 9,9-dimethylfluorenyl group, or a dibenzofuranyl group and Ar 11 is a phenyl group substituted with a monocyclic group or a condensed ring group.
  • Ar 12 is a condensed ring group and Ar 11 is an unsubstituted phenyl group.
  • the condensed ring group is especially preferably a phenanthryl group, a 9,9-dimethylfluorenyl group, a dibenzofuranyl group, or a benzoanthryl group.
  • the subject anthracene derivative is one represented by the formula (4) wherein each of Ar 11 and Ar 12 independently represents a substituted or unsubstituted monocyclic group having 5 to 50 ring atoms.
  • a preferred embodiment is one in which both of Ar 11 and Ar 12 are substituted or unsubstituted phenyl groups.
  • Ar 11 is an unsubstituted phenyl group and Ar 12 is a phenyl group substituted by a monocyclic group or a condensed ring group and the case where each of Ar 11 and Ar 12 independently represents a phenyl group substituted by a monocyclic group or a condensed ring group.
  • examples of the monocyclic group and the condensed ring group which are preferable as the substituent are those described above. More preferably, examples of the monocyclic ring as the substituent include a phenyl group and a biphenyl group; and examples of the condensed ring group as the substituent include a naphthyl group, a phenanthryl group, a 9,9-dimethylfluorenyl group, a dibenzofuranyl group, and a benzoanthryl group.
  • the pyrene derivative represented by the formula (5) is the following compound:
  • each of Ar 111 and Ar 222 independently represents a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.
  • Each of the L 101 and L 102 independently represents a substituted or unsubstituted divalent aryl group having 6 to 30 ring carbon atoms or a heterocyclic group.
  • L 101 or Ar 111 is bonded at any of 1- to 5-positions of pyrene and L 102 or Ar 222 is bonded at any of 6- to 10-positions of pyrene.
  • each of L 101 and L 102 is preferably a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted fluorenylene group, or a divalent aryl group composed of a combination of these substituents.
  • each of L 101 and L 102 is preferably an alkyl group having 1 to 20 carbon atoms.
  • m is preferably an integer of 0 to 1.
  • n is preferably an integer of 1 to 2.
  • s is preferably an integer of 0 to 1.
  • t is preferably an integer of 0 to 2.
  • the aryl group of each of Ar 111 and Ar 222 is the same as those in the formula (1).
  • the aryl group is preferably a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms, and more preferably a substituted or unsubstituted aryl group having 6 to 16 ring carbon atoms.
  • Preferred specific examples of the aryl group include a phenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group, a biphenyl group, an anthryl group, and a pyrenyl group.
  • the light emitting layer containing the anthracene derivative represented by the formula (4) or the pyrene derivative represented by the formula (5) preferably comes into contact with the blocking layer containing the benzo[k]fluoranthene derivative of the invention, the electron injecting layer, or the electron transporting layer.
  • the light emitting layer comes into contact with the blocking layer containing the benzo[k]fluoranthene derivative of the invention, the electron injecting layer, or the electron transporting layer, the luminous efficiency can be enhanced utilizing the TTF phenomenon.
  • the light emitting layer may contain a light emitting dopant (phosphorescent dopant and/or fluorescent dopant).
  • the fluorescent dopant is a compound capable of causing light emission from a singlet exciton.
  • the fluorescent dopant is preferably a compound which is selected in conformity with the required luminescent color among an amine based compound, an aromatic compound, a chelate complex, such as a tris(8-quinolinolato)aluminum complex, a coumarin derivative, a tetraphenylbutadiene derivative, a bisstyrylarylene derivative, an oxadiazole derivative, and the like.
  • a styrylamine compound, a styryldiamine compound, an arylamine compound, an aryldiamine compound, and an aromatic compound are more preferable, and a condensed polycyclic amine derivative and an aromatic compound are still more preferable.
  • These fluorescent dopants may be used singly or in combination of plural kinds thereof.
  • the condensed polycyclic amine derivative is preferably one represented by the following formula (12):
  • Y represents a substituted or unsubstituted condensed aryl group having 10 to 50 ring carbon atoms.
  • Each of Ar 101 and Ar 102 represents a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
  • Y include those described above regarding the condensed aryl group, and preferred examples thereof include a substituted or unsubstituted anthryl group, a substituted or unsubstituted pyrenyl group, and a substituted or unsubstituted chrysenyl group.
  • each of Ar 101 and Ar 102 include those described above regarding the aryl group or heterocyclic group, and preferred examples thereof include a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, and a substituted or unsubstituted dibenzofuranyl group.
  • n is an integer of 1 to 4 and preferably an integer of 1 to 2.
  • examples of the alkyl group, the alkoxy group, the aryl group, the aryloxy group, and the heterocyclic group include those exemplified above.
  • the aromatic compound is preferably a benzo[k]fluoranthene compound represented by the following formula (13):
  • each of X 301 to X 306 and X 308 to X 311 is independently selected from a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 8 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms, a substituted or unsubstituted
  • Each of X 307 and X 312 is independently selected from a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and a substituted or unsubstituted cycloalkyl group having 3 to 8 ring carbon atoms.
  • X 303 and X 304 are different.
  • the adjoining substituents may be bonded to each other to form a saturated or unsaturated cyclic structure, and such a cyclic structure may be substituted.
  • X 301 or X 304 in the formula (13) is preferably a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms. Also, the substituent of the terms "substituted or unsubstituted" in the formula (13) is preferably a cyano group or a halogen atom.
  • examples of each of the aryl group, the heterocyclic group, the alkyl group, the cycloalkyl group, the alkoxy group, the aralkyl group, the aryloxy group, the arylthio group, the alkoxycarbonyl group, and the halogen atom include those exemplified above.
  • the dopant is preferably a dopant exhibiting fluorescent light emission, a main peak wavelength of which is not more than 550 nm, and more preferably a blue light emitting dopant.
  • the main peak wavelength refers to a peak wavelength of light emitting spectrum at which a light emission intensity becomes maximum in the light emitting spectrum, and the main peak wavelength of 550 nm is corresponding to a green light emission.
  • an enhancement of the luminous efficiency of a fluorescent light emitting device utilizing the TTF phenomenon is desired.
  • a fluorescent light emitting device exhibiting blue light emission of not more than 480 nm a higher enhancement of the luminous efficiency can be expected.
  • organic EL device of the present invention such as the substrate, the anode, the cathode, the hole injecting layer, the hole transporting layer, and the like can be properly selected and used among those which are known, as described in WO2008/023759A1 , WO2008/023759A1 , WO2009/107596A1 , WO2009/081857A1 , US2009/0243473A1 , US2008/0014464A1 , US2009/0021160A1 , and the like.
  • a compound was synthesized in the same manner as in Example 1, except for using 2-(4'-bromophenyl)-1,10-phenanthroline in place of 6-bromo-2,2'-bipyridine.
  • a compound was synthesized in the same manner as in Example 1, except for using 4-(4-bromophenyl)-2-phenyl-6-(2-pyridyl)pyrimidine in place of 6-bromo-2,2'-bipyridine.
  • the " ⁇ edge" means a wavelength value at the point of intersection of a tangent line with the horizontal axis, the tangent line being drawn in a rising portion on the short wavelength side of the phosphorescent spectrum. Unit: nm.
  • the ionization potential was measured under the surrounding atmosphere using a photoelectron spectrometer (AC-3, manufactured by Riken Keiki Co., Ltd.). Specifically, light was irradiated on the material, and on that occasion, a quantity of electron generated by charge separation was measured, thereby determining the ionization potential.
  • AC-3 photoelectron spectrometer
  • the affinity was calculated from the measured values of ionization potential and energy gap.
  • the energy gap was measured from an absorption end of the absorption spectrum of a toluene solution of Compound 1 or 2. Specifically, an absorption spectrum was measured using a commercially available visible light/ultraviolet spectrophotometer, and the affinity was calculated from a wavelength (absorption end) at which the spectrum started to rise up.
  • Table 1 Triplet energy (eV) Ionization potential (eV) Affinity (eV) Compound 1 2.1 6.0 3.2 Compound 2 2.1 6.0 3.2 Compound 3 2.1 6.0 3.2
  • a glass substrate provided with an ITO transparent electrode (anode) having a size of 25 mm x 75 mm and a thickness of 1.1 mm was subjected to ultrasonic cleaning in isopropyl alcohol for 5 min and then subjected to UV ozone cleaning for 30 min.
  • the thus cleaned transparent electrode line-provided glass substrate was installed in a substrate holder of a vacuum vapor deposition apparatus, and Compound HT-1 was deposited so as to cover the transparent electrode line to form a film having a thickness of 50 nm.
  • the HT-1 film functions as a hole injecting layer.
  • Compound HT-2 was vapor deposited, thereby forming an HT-2 film having a thickness of 45 nm on the HT-1 film.
  • the HT-2 film functions as a hole transporting layer.
  • Compound BH-1 (host material) and Compound BD-1 (dopant material) were vapor deposited in a film thickness ratio of 20:1 on the HT-2 film, thereby forming an organic layer having a thickness of 25 nm.
  • This organic layer functions as a light emitting layer.
  • Compound 1 was vapor deposited on the light emitting layer, thereby forming an electron transporting layer having a film thickness of 25 nm. Thereafter, LiF was deposited in a film thickness of 1 nm.
  • Metallic Al was vapor deposited in a thickness of 80 nm on this LiF film to form a metal cathode, thereby fabricating an organic EL light emitting device.
  • a glass substrate provided with an ITO transparent electrode (anode) having a size of 25 mm x 75 mm and a thickness of 1.1 mm was subjected to ultrasonic cleaning in isopropyl alcohol for 5 min and then subjected to UV ozone cleaning for 30 min.
  • the thus cleaned transparent electrode line-provided glass substrate was installed in a substrate holder of a vacuum vapor deposition apparatus, and Compound HT-1 was deposited so as to cover the transparent electrode line, thereby forming a film having a thickness of 50 nm.
  • the HT-1 film functions as a hole injecting layer.
  • Compound HT-2 was vapor deposited, thereby forming an HT-2 film having a thickness of 45 nm on the HT-1 film.
  • the HT-2 film functions as a hole transporting layer.
  • Compound BH-1 (host material) and Compound BD-1 (dopant material) were vapor deposited in a film thickness ratio of 20:1 on the HT-2 film, thereby forming a light emitting layer having a thickness of 25 nm.
  • Compound 1 and lithium quinolinolate (Liq) were vapor deposited in a film thickness ratio of 1:1 on the light emitting layer, thereby forming an electron transporting layer in a film thickness of 25 nm on the light emitting layer.
  • Metallic Al was vapor deposited in a thickness of 80 nm on this electron transporting layer to form a metal cathode, thereby fabricating an organic EL device.
  • the resulting organic EL device was evaluated in the same manners as in Example 3. The results are shown in Table 3.
  • Example 7 Compound 1 + Liq BD-1 3.5 8.8 Blue 750
  • Example 8 Compound 2 + Liq BD-1 3.3 8.1 Blue 250
  • Example 9 Compound 3 + Liq BD-1 3.6 8.2 Blue 200
  • Example 10 Compound 1 + Liq BD-2 3.6 7.7 Blue 190 Comparative Example 3 ET-1 + Liq BD-1 3.7 8.3 Blue 70 Comparative Example 4 ET-2 + Liq BD-1 4.6 7.7 Blue 40
  • the affinity (Af) of the benzofluoranthene ring is large, the driving voltage is low even when the electron transporting layer is a co-vapor deposited layer with lithium quinolate.
  • the effect of a blocking material may be attributable to the high luminous efficiency achieved by each of Compounds 1 to 3.
  • the triplet energy of the host material BH-1 is 1.8 eV when calculated in the same manner as in each of Compounds 1 to 3. Since the triplet energies of Compounds 1 to 3 is a sufficiently large as compared with that of BH-1, it can be considered that the triplet exciton is effectively confined within the light emitting layer.
  • the organic EL device containing the benzo[k]fluoranthene derivative of the present invention can be used for display panels for large-sized television, illumination panels, and the like, which are desired to reduce the electric power consumption.

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Claims (10)

  1. Ein Benzo[k]fluoranthen-Derivat dargestellt durch die folgende Formel (1):
    Figure imgb0151
     wobei die Reste R1 bis R12 jeweils unabhängig voneinander ein Wasserstoffatom, ein Halogenatom, eine substituierte oder unsubstituierte Alkylgruppe mit 1 bis 10 Kohlenstoffatomen, eine substituierte oder unsubstituierte Cycloalkylgruppe mit 3 bis 8 Ringkohlenstoffatomen, eine substituierte Silylgruppe mit 3 bis 30 Kohlenstoffatomen, eine Cyanogruppe, eine substituierte oder unsubstituierte Alkoxygruppe mit 1 bis 20 Kohlenstoffatomen, eine substituierte oder unsubstituierte Aryloxygruppe mit 6 bis 20 Ringkohlenstoffatomen, eine substituierte oder unsubstituierte Arylgruppe mit 6 bis 30 Ringkohlenstoffatomen, oder eine substituierte oder unsubstituierte heterocyclische Gruppe mit 5 bis 30 Ringatomen darstellen;
    mit der Maßgabe, dass mindestens einer der Reste R1 bis R12 eine durch die folgende Formel (1a) dargestellte Gruppe ist:

            -L(̵HAr)n     (1a)

    wobei L eine Einfachbindung, einen zweiwertigen bis vierwertigen Rest eines substituierten oder unsubstituierten aromatischen Kohlenwasserstoffrings mit 6 bis 30 Ringkohlenstoffatomen, einen zweiwertigen bis vierwertigen Rest eines substituierten oder unsubstituierten heterocyclischen Rings mit 5 bis 30 Ringatomen, oder einen zweiwertigen bis vierwertigen Rest eines Rings, gebildet durch Verbindung von 2 bis 3 Ringen ausgewählt aus dem aromatischen Kohlenwasserstoffring und dem heterocyclischen Ring über eine Einfachbindung darstellt;
    n eine ganze Zahl von 1 bis 3 darstellt; und
    HAr eine Gruppe, dargestellt durch die folgende Formel (2), darstellt:
    Figure imgb0152
    wobei X1 bis X8 jeweils unabhängig voneinander ein Stickstoffatom oder CR13 darstellen, und mindestens eines von X1 bis X8 CR13 ist;
    jeder der Reste R13 unabhängig voneinander ein Wasserstoffatom, ein Halogenatom, eine substituierte oder unsubstituierte Alkylgruppe mit 1 bis 10 Kohlenstoffatomen, eine substituierte oder unsubstituierte Cycloalkylgruppe mit 3 bis 8 Ringkohlenstoffatomen, eine substituierte Silylgruppe mit 3 bis 30 Kohlenstoffatomen, eine Cyanogruppe, eine substituierte oder unsubstituierte Alkoxygruppe mit 1 bis 20 Kohlenstoffatomen, eine substituierte oder unsubstituierte Aryloxygruppe mit 6 bis 20 Ringkohlenstoffatomen, eine substituierte oder unsubstituierte Alkylthiogruppe mit 1 bis 20 Kohlenstoffatomen, eine substituierte oder unsubstituierte Mono- oder Dialkylaminogruppe mit 1 bis 20 Kohlenstoffatomen, eine substituierte oder unsubstituierte Arylgruppe mit 6 bis 30 Ringkohlenstoffatomen, eine substituierte oder unsubstituierte heterocyclische Gruppe mit 5 bis 30 Ringatomen, eine substituierte oder unsubstituierte Arylthiogruppe mit 6 bis 20 Ringkohlenstoffatomen, oder eine substituierte oder unsubstituierte Mono- oder Diarylaminogruppe mit 6 bis 40 Ringkohlenstoffatomen darstellt;
    mit der Maßgabe, dass einer der Reste R13 eine Einfachbindung ist und an L gebunden ist;
    zwei oder mehr der Reste R13 aneinander gebunden sein können unter Bildung einer substituierten oder unsubstituierten, gesättigten oder ungesättigten Gruppe; und
    der Fall, wobei X4 und X5 jeweils CR13 sind und die Reste R13 aneinander unter Bildung einer gesättigten oder ungesättigten Methylengruppe gebunden sind, ausgeschlossen ist; und
    wobei der optionale Substituent, bezeichnet mit "substituiert oder unsubstituiert", aus einem Halogenatom, einer substituierten oder unsubstituierten Alkylgruppe mit 1 bis 10 Kohlenstoffatomen, einer substituierten oder unsubstituierten Cycloalkylgruppe mit 3 bis 8 Ringkohlenstoffatomen, einer substituierten oder unsubstituierten Silylgruppe mit 3 bis 30 Kohlenstoffatomen, einer Cyanogruppe, einer substituierten oder unsubstituierten Alkoxygruppe mit 1 bis 20 Kohlenstoffatomen, einer substituierten oder unsubstituierten Aryloxygruppe mit 6 bis 20 Ringkohlenstoffatomen, einer substituierten oder unsubstituierten Alkylthiogruppe mit 1 bis 20 Kohlenstoffatomen, einer substituierten oder unsubstituierten Mono- oder Dialkylaminogruppe mit 1 bis 20 Kohlenstoffatomen, einer substituierten oder unsubstituierten Arylgruppe mit 6 bis 30 Ringkohlenstoffatomen, und einer substituierten oder unsubstituierten heterocyclischen Gruppe mit 5 bis 30 Ringatomen ausgewählt ist.
  2. Das Benzo[k]fluoranthen-Derivat gemäß Anspruch 1, wobei HAr einer der stickstoffhaltigen heterocyclischen Ringe, dargestellt durch die folgenden Formeln (3) bis (7), ist:
    Figure imgb0153
    Figure imgb0154
    wobei die Reste R21 bis R66 jeweils unabhängig voneinander ein Wasserstoffatom, ein Halogenatom, eine substituierte oder unsubstituierte Alkylgruppe mit 1 bis 10 Kohlenstoffatomen, eine substituierte oder unsubstituierte Cycloalkylgruppe mit 3 bis 8 Ringkohlenstoffatomen, eine substituierte Silylgruppe mit 3 bis 30 Kohlenstoffatomen, eine Cyanogruppe, eine substituierte oder unsubstituierte Alkoxygruppe mit 1 bis 20 Kohlenstoffatomen, eine substituierte oder unsubstituierte Aryloxygruppe mit 6 bis 20 Ringkohlenstoffatomen, eine substituierte oder unsubstituierte Alkylthiogruppe mit 1 bis 20 Kohlenstoffatomen, eine substituierte oder unsubstituierte Mono- oder Dialkylaminogruppe mit 1 bis 20 Kohlenstoffatomen, eine substituierte oder unsubstituierte Arylgruppe mit 6 bis 30 Ringkohlenstoffatomen, eine substituierte oder unsubstituierte heterocyclische Gruppe mit 5 bis 30 Ringatomen, eine substituierte oder unsubstituierte Arylthiogruppe mit 6 bis 20 Ringkohlenstoffatomen, oder eine substituierte oder unsubstituierte Mono- oder Diarylaminogruppe mit 6 bis 40 Ringkohlenstoffatomen darstellen;
    in Formel (3) zwei oder mehr der Reste R21 bis R28 aneinander unter Bildung einer ringbildenden substituierten oder unsubstituierten, gesättigten oder ungesättigten Gruppe gebunden sein können, mit der Maßgabe, dass einer der Reste R21 bis R28 eine Einfachbindung ist und an L gebunden ist, und der Fall, dass die Reste R24 und R25 aneinander unter Bildung einer substituierten oder unsubstituierten Methylengruppe gebunden sind, ausgeschlossen ist;
    in Formel (4) zwei oder mehr der Reste R31 bis R38 aneinander unter Bildung einer ringbildenden substituierten oder unsubstituierten, gesättigten oder ungesättigten Gruppe gebunden sein können, mit der Maßgabe, dass einer der Reste R31 bis R38 eine Einfachbindung ist und an L gebunden ist;
    in Formel (5) zwei oder mehr der Reste R41 bis R47 aneinander unter Bildung einer ringbildenden substituierten oder unsubstituierten, gesättigten oder ungesättigten Gruppe gebunden sein können, mit der Maßgabe, dass einer der Reste R41 bis R47 eine Einfachbindung ist und an L gebunden ist;
    in Formel (6) zwei oder mehr der Reste R51 bis R57 aneinander unter Bildung einer ringbildenden substituierten oder unsubstituierten, gesättigten oder ungesättigten Gruppe gebunden sein können, mit der Maßgabe, dass einer der Reste R51 bis R57 eine Einfachbindung ist und an L gebunden ist, und der Fall, wobei die Reste R53 und R54 aneinander unter Bildung einer substituierten oder unsubstituierten Methylengruppe gebunden sind, ausgeschlossen ist; und
    in Formel (7) zwei oder mehr der Reste R61 bis R66 aneinander unter Bildung einer ringbildenden substituierten oder unsubstituierten, gesättigten oder ungesättigten Gruppe gebunden sein können, mit der Maßgabe, dass einer der Reste R61 bis R66 eine Einfachbindung ist und an L gebunden ist, und
    wobei der optionale Substituent, bezeichnet mit "substituiert oder unsubstituiert", aus einem Halogenatom, einer substituierten oder unsubstituierten Alkylgruppe mit 1 bis 10 Kohlenstoffatomen, einer substituierten oder unsubstituierten Cycloalkylgruppe mit 3 bis 8 Ringkohlenstoffatomen, einer substituierten oder unsubstituierten Silylgruppe mit 3 bis 30 Kohlenstoffatomen, einer Cyanogruppe, einer substituierten oder unsubstituierten Alkoxygruppe mit 1 bis 20 Kohlenstoffatomen, einer substituierten oder unsubstituierten Aryloxygruppe mit 6 bis 20 Ringkohlenstoffatomen, einer substituierten oder unsubstituierten Alkylthiogruppe mit 1 bis 20 Kohlenstoffatomen, einer substituierten oder unsubstituierten Mono- oder Dialkylaminogruppe mit 1 bis 20 Kohlenstoffatomen, einer substituierten oder unsubstituierten Arylgruppe mit 6 bis 30 Ringkohlenstoffatomen, und einer substituierten oder unsubstituierten heterocyclischen Gruppe mit 5 bis 30 Ringatomen ausgewählt ist.
  3. Das Benzo[k]fluoranthen-Derivat gemäß Anspruch 1 oder 2, welches durch die folgende Formel (8) dargestellt ist:
    Figure imgb0155
     wobei R1 bis R3, R5 bis R12, HAr, L und n wie in Formel (1) definiert sind.
  4. Das Benzo[k]fluoranthen-Derivat gemäß einem der Ansprüche 1 bis 3, wobei n 1 ist.
  5. Ein Material für eine organische Elektrolumineszenz-Vorrichtung, umfassend das Benzo[k]fluoranthen-Derivat gemäß einem der Ansprüche 1 bis 4.
  6. Das Material für eine organische Elektrolumineszenz-Vorrichtung gemäß Anspruch 5, wobei das Material ein elektroneninjizierendes Material oder ein elektronentransportierendes Material ist.
  7. Eine organische Elektrolumineszenz-Vorrichtung, umfassend eine oder mehrere organische Dünnfilmschichten, welche eine lichtemittierende Schicht umfassen und zwischen einer Kathode und einer Anode eingefügt sind, wobei mindestens eine Schicht der organischen Dünnfilmschichten eine oder mehrere Arten des Benzo[k]fluoranthen-Derivats gemäß einem der Ansprüche 1 bis 4 umfasst.
  8. Die organische Elektrolumineszenz-Vorrichtung gemäß Anspruch 7, wobei die organische Dünnfilmschicht eine elektroneninjizierende Schicht oder eine elektronentransportierende Schicht umfasst, und die elektroneninjizierende Schicht oder die elektronentransportierende Schicht eine oder mehrere Arten des Benzo[k]fluoranthen-Derivats gemäß einem der Ansprüche 1 bis 4 umfasst.
  9. Die organische Elektrolumineszenz-Vorrichtung gemäß Anspruch 8, wobei die elektroneninjizierende Schicht oder die elektronentransportierende Schicht, umfassend das Benzo[k]fluoranthen-Derivat, weiter ein reduzierendes Dotierungsmittel umfasst.
  10. Die organische Elektrolumineszenz-Vorrichtung gemäß Anspruch 9, wobei das reduzierende Dotierungsmittel eine oder mehrere Arten ausgewählt aus der Gruppe bestehend aus einem Alkalimetall, einem Erdalkalimetall, einem Seltenerdmetall, einem Alkalimetalloxid, einem Alkalimetallhalogenid, einem Erdalkalimetalloxid, einem Erdalkalimetallhalogenid, einem Seltenerdmetalloxid, einem Seltenerdmetallhalogenid, einem organischen Komplx eines Alkalimetalls, einem organischen Komplex eines Erdalkalimetalls und einem organischen Komplex eines Seltenerdmetalls ist.
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EP2626346A4 (de) 2014-03-19
US20120211743A1 (en) 2012-08-23
EP2626346A1 (de) 2013-08-14
US9273002B2 (en) 2016-03-01
KR101429832B1 (ko) 2014-08-12
CN102574797B (zh) 2017-03-01
CN102574797A (zh) 2012-07-11
KR20130025858A (ko) 2013-03-12
WO2012046839A1 (ja) 2012-04-12
JPWO2012046839A1 (ja) 2014-02-24
TW201215659A (en) 2012-04-16
JP5909179B2 (ja) 2016-04-26

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